New synthetic methodology for the formation of trans-1,4-cyclopentenols and cyclohexenols has been developed from cyanocuprate reactions of cyclic 1,3-epoxyalkenes. This basic reaction is highly regiospecific and stereospecific and can be used to introduce additional functional groups in successive reactions. Unique synthetic routes to substituted epoxy cyclohexenes, cyclopentenes and cycloheptenes have been realized. This work has also led to very efficient syntheses of acyclic chiral molecules containing three centers of asymmetry and offers promise for the efficient generation of new prostanoid analogs as potential antitumor agents. The reactions studied to date are being applied to the synthesis of modified steroids, prostanoids and other lipophilic natural products which will contain reactive epoxyacrylate, hydroxymethylacrylate and masked keto-acrylate units.